Synthesis, Antibacterial, Antifungal and Antiviral Activity Evaluation of Some New bis-Schiff Bases of Isatin and Their Derivatives

Abstract

Twelve new bis-Schiff bases of isatin, benzylisatin and 5-fluoroisatin 3a-3l were prepared by condensation of isatin, benzylisatin and 5-fluoroisatin with primary aromatic amines. The chemical structures of the products were confirmed by 1H- and 13CNMR, IR and mass spectral data. The compounds were screened for antiviral activity against a panel of DNA and RNA viruses. Minimum cytotoxic and minimum virus-inhibitory concentrations of these compounds were determined. Compounds 3c and 3i were the most cytotoxic in HEL cells. These newly synthesized bis-Schiff bases were also tested for their antibacterial and antifungal activities. They did not display activity against S. cerevisiae (ATCC 28383) or C. albicans (CIP 1180-79).

A facile green chemistry approaches towards the synthesis of bis-Schiff bases using ultrasound versus microwave and conventional method without catalyst

“…A similar situation was observed from the melting points of these bis-Schiff bases: melting point of 4d is lower than those of the other compounds (See experimental section). In the 13 C NMR spectra of the bis-Schiff bases 3-5, the carbon atoms of the azomethine groups were shown in the 166.7-158.3 ppm range. Moreover, the structures of all bis-Schiff bases 3-5 were further confirmed by mass spectra (MS) and elemental analyses.…”

“…IR spectra were recorded on a PerkinElmer Spectrum One spectrometer, using samples prepared as KBr discs. 1 H, 13 C and 19 F NMR spectra were recorded at 400,100 and 376 MHz, respectively. Chemical shifts (δ) are reported in ppm, using the residual solvent CDCl 3 δ (H) = 7.26 and δ (C) = 77.16; DMSO-d 6 δ (H) = 2.50 and δ(C) = 39.52) as internal standard.…”

1-Propyl-1H-indole-2,3-dione

“…Isatin is a core constituent of many alkaloids (Batanero & Barba, 2006) and drugs (Aboul-Fadl et al, 2010) as well as dyes (Domé nech et al, 2009), pesticides and analytical reagents. Various derivatives of isatin show diverse biological activities including antibacterial (Kassab et al, 2010), antifungal (Amal Raj et al, 2003, antiviral (Jarrahpour et al, 2007), anti-HIV (Bal et al, 2005), anti-mycobacterial (Karalı et al, 2007), anticancer (Gü rsoy & Karalı 2003), and anti-inflammatory activities (Sridhar & Ramesh 2001) and are also effective anticonvulsants (Verma et al 2004). Furthermore, isatin derivatives with their multifunctionality and diversity of transformations are synthetically versatile substrates and many efforts have been made toward the synthesis of these compounds.…”

Synthesis, Characterization and DPPH Scavenging Assay of Isatin Related Spiroheterocyclic Compounds

“…Isatin (1-H-indole-2,3-dione) and its derivatives possess diverse biological and pharmacological activities and are widely used as a starting material for the synthesis of a broad range of heterocyclic compound substrates for drug synthesis [1] . Isatin is a heterocyclic compound and derivatives of isatin possess biological activities such as antimicrobial [2] , antibacterial, antifungal [3] , antiviral [4] , antiHIV [5] , anticancer [6,7] , antiproliferative [8] , antioxidant activity [9] . Spirocyclic systems containing one common carbon atom to two rings are structurally interesting [10] and naturally occurring substances being known for their wide range of biological activities [11,12] .…”